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Emmy Rossum
From 2009 to 2010 (Relationship)
Whitney Casey
From 2008 to 2008 (Relationship)
Trishelle Cannatella
From 2006 to 2006 (Relationship)
Samantha Mathis
From 2004 to 2005 (Relationship)
Mary-Louise Parker
From 1997 to 1998 (Relationship)
Courteney Cox
From 1997 to 1997 (Relationship)
Jennifer Aniston
From 1995 to 1995 (Rumored Relationship)
Winona Ryder
From 1994 to 1995 (Rumored Encounter)
Joanna Going
(Rumored )
Monica Potter
(Relationship)
Lara Flynn Boyle
(Rumored Relationship)
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